A festive, practical guide to year-end calm and a strong New Year rooted in Fractional CFO, accounting, and tax planning & filing.
Quick wrap (for the busy founders)
Twelve everyday, do-right-now tips across cash flow, bookkeeping, tax planning, and CFO strategy each with a 10-minute action, a KPI to watch, and how a CleverProfits fractional CFO, accounting team, or tax specialist can help.
Tip 1: A Cash-Flow Partridge in a Pear Tree
Theme: Short-term liquidity beats year-end surprises.
Do this today (10 minutes): Open your cash forecast and extend it through January 31. Add payroll, rent, debt service, sales tax, and expected collections.
KPI: Weeks of cash on hand (target 4 – 8 weeks depending on seasonality).
Why it matters: December receipts slow; January compresses everything. A simple, rolling forecast turns anxiety into clarity.
How Clever helps: A Fractional CFO builds a dynamic model, tests late-payment scenarios, and sets a line-of-credit strategy so you go into Q1 with confidence.
Tip 2: Two Invoices Flying (Out the Door)
Theme: Collections without the cringe.
Do this today: Turn on automated AR reminders at 7/14/21 days; include ACH/CC links. Send a friendly “year-end tidy-up” note to open balances.
KPI: % of AR >30 days and weekly cash collected.
Why it matters: One reminder sequence can pull forward a week of runway.
How Clever helps: Accounting & Bookkeeping team implements smart dunning, reconciles receipts quickly, and your CFO sets incentive offers that don’t erode margin.
Tip 3: Three Clean Recons
Theme: Reconcile banks/credit cards before you log off.
Do this today: Reconcile through the latest statement; flag unmatched items; lock the GL through the last reconciled date.
KPI: Reconciliation staleness (days since last recon).
Why it matters: Clean books now = faster tax close, clearer decisions in January.
How Clever helps: Accounting closes November/December fast, maintains audit trails, and prevents stray edits with close controls.
Tip 4: Four Payroll Drumbeats
Theme: No payroll surprises over holidays.
Do this today: Confirm next two payroll dates, funding cutoffs, bonus runs, and time-off accrual policies. Put dates in a shared calendar.
KPI: Payroll funded on time (100%).
Why it matters: Holiday bank closures + bonuses can create cash timing hiccups.
How Clever helps: Accounting schedules runs and uses a CFO-approved cash calendar to keep payroll, bonuses, and vendor payments in sync.
Tip 5: Five Golden Controls
Theme: Prevent “oops” spending while you’re away.
Do this today: Enable dual approval for bill pay, restrict corporate card limits, enforce MFA on finance apps, and review admin access.
KPI: % of bills paid with dual approval, # of admins (keep minimal).
Why it matters: The cheapest fraud is the fraud that never happens.
How Clever helps: Fractional CFO + Accounting design your approval matrix and spending guardrails; Tax flags deductible vs. nondeductible items.
Tip 6: Six Sales a-Gleaming (in Pipeline)
Theme: Don’t let January start from zero.
Do this today: Tag “Warm-January” opportunities. Schedule re-activation emails for first week back with one-click booking links.
KPI: Next-meeting rate on stalled deals, pipeline coverage (≥3× target).
Why it matters: A gentle nudge pre-holiday creates a full first-two-weeks calendar.
How Clever helps: Fractional CFO ties pipeline to revenue capacity and hiring plan; we quantify where to invest for highest return.
Tip 7: Seven Vendors Syncing
Theme: Keep suppliers aligned to your holiday cadence.
Do this today: Email top vendors your AP run dates, receiving/ship windows, and emergency contact. Batch noncritical invoices to the first full week of January.
KPI: On-time pay rate and early-pay savings captured.
Why it matters: Clear expectations avoid service hiccups and late fees.
How Clever helps: Accounting sets up scheduled payments; CFO validates early-pay discounts vs. cash cost.
Tip 8: Eight W-9s a-Waiting
Theme: 1099s and W-2s are won in December.
Do this today: Pull vendor list; request missing W-9s; confirm contractor emails and addresses. Verify employee addresses in payroll.
KPI: % of 1099-eligible vendors with W-9 on file (target 100%).
Why it matters: January 31 filing comes fast; prep now to avoid scramble.
How Clever helps: Tax Planning & Filing automates requests, prepares 1099s/W-2s, and reconciles to your GL to minimize corrections.
Tip 9: Nine Deductions Dancing
Theme: Last-minute, smart tax planning—no gimmicks.
Do this today: Review capex, prepaid expenses, retirement plan contributions, and bonus timing with your CPA. Model buy-now vs. defer.
KPI: Effective tax rate vs. target and cash impact.
Why it matters: Timing matters; deductions should serve your strategy, not just the calendar.
How Clever helps: Tax Planning coordinates with your CFO to align deductions, entity elections, and owner distributions with cash and growth goals.
Tip 10: Ten KPIs a-Leaping
Theme: A tiny year-end dashboard you’ll actually read.
Do this today: Set 5–7 metrics with red/yellow/green thresholds: Cash on hand, weekly collections, AR>30, payroll status, on-time shipments, open tickets, and a lead indicator (new demos booked).
KPI: (Meta!) % of weeks with green status on the dashboard.
Why it matters: If you only check once a week, make it count.
How Clever helps: Fractional CFO builds the dashboard, wires alerts, and runs a January retro to tighten thresholds.
Tip 11: Eleven Emails Sleeping (OOO Done Right)
Theme: Communicate once; prevent 100 follow-ups.
Do this today: Publish holiday hours on your site/support widget, set OOO with an on-call contact, and send “holiday checkpoint” emails for open projects: status, next step, return date.
KPI: % of customer inquiries answered within SLA, # duplicate tickets (aim down).
Why it matters: Expectations reduce escalations; escalations kill holidays.
How Clever helps: Accounting and CFO coordinate customer credits/SLAs where needed and ensure the financial impact is tracked.
Tip 12: Twelve Weeks of Runway
Theme: Start January with a Q1 plan you’re proud of.
Do this today: Book a 60-minute January Re-Start: re-forecast through March, set 1–3 quarterly outcomes, and define weekly owner scorecards.
KPI: Q1 plan on one page shared with owners/leads.
Why it matters: Momentum loves clarity.
How Clever helps: Fractional CFO turns ambition into a cash-aware operating plan; Accounting closes books fast so you can measure progress; Tax preps deadlines so compliance doesn’t derail execution.
The Print-Friendly Checklist (to use with your team)
Cash & CFO
- Extend cash forecast to Jan 31 (add payroll, rent, debt, tax).
- Confirm LOC availability and card limits.
- Approve early-pay discounts (if ROI > borrowing cost).
- Schedule January Re-Start planning session.
Accounting
- Reconcile bank/credit cards through latest statement.
- Lock the GL through last reconciled date; export a backup.
- Turn on AR reminders; enable ACH/CC payments.
- Schedule AP runs (pre-holiday and first full week of January).
Tax
- Pull 1099-eligible vendor list; collect W-9s.
- Verify employee addresses; preview W-2 data.
- Model capex/bonus timing; confirm Q4 estimates (often due Jan 15).
- List January state/sales-tax filings with due dates.
Operations & Customers
- Publish holiday hours and SLAs.
- Send project “checkpoint” emails with on-call contacts.
- Confirm last ship dates; update checkout messages.
- Set OOO across email/Slack with who’s covering what.
Security & Controls
- MFA on all finance apps; audit admin roles.
- Dual approvals for bill pay; temporary card limits.
- Device encryption/VPN for anyone traveling.
Dashboard (Weekly)
- Cash on hand (weeks), weekly collections, AR>30, payroll status, on-time shipments, open tickets, demos booked.
- Define R/Y/G thresholds and who gets alerted.
How this ties back to our services
- Fractional CFO Services: Cash forecasting, KPI dashboards, controlled spend frameworks, pricing & pipeline planning, Q1 operating plan.
- Accounting & Bookkeeping: Reconciliations, close process, AP/AR automation, payroll coordination, clean audit trails.
- Tax Planning & Filing: Year-end optimization (timing of deductions), 1099/W-2 workflows, sales/use tax calendars, owner-level estimates.
The gift here isn’t a cute metaphor, it’s clarity and control. With our CFO’s, accountants, and tax pro’s aligned, you get a holiday you can actually enjoy and a January that feels composed, not chaotic.
FAQ’s
What should I do first if I only have 30 minutes?
Update your cash forecast through Jan 31 and turn on AR reminders with quick-pay links. Those two actions change outcomes fastest.
How much cash buffer should I hold over the holidays?
Aim for 4 – 8 weeks of operating expenses. If customers typically pay late in December/early January, lean toward the higher end.
Do I have to send 1099s to every vendor?
No. Generally you’ll send 1099-NEC to non-employee service providers paid $600+, with exceptions. Always collect W-9s and confirm with your tax professional.
What KPIs matter if I only check once a week?
Cash on hand (weeks), weekly collections, AR>30, payroll status, support backlog, and one lead indicator (e.g., demos booked).
What’s the fastest way to reduce year-end stress?
Set dual approval for payables, pre-schedule AP runs, confirm payroll funding dates, and publish holiday hours with on-call contacts.
Give yourself the gift of a quiet holiday (and a powerful Q1)
Ready to put these 12 tips on autopilot? Our Fractional CFOs, accountants, and tax pros will build your cash forecast, clean your books, and prep 1099/W-2 filings so you can actually unplug.
Book a call with CleverProfits and start January strong.
The Clever Writing Team
The CleverProfits writing team includes various team members in Advisory, Financial Strategy, Tax, and Leadership. Our goal is to provide relevant and easy-to-understand financial content to help founders and business leaders reach their true potential.
TABLE OF CONTENTS
- 1099 prep checklist, 1099-NEC, AP/AR automation, AR reminders, cash flow forecast template, cash runway, dual approval, fractional CFO holiday checklist, GL lock date, holiday finance tips for small business, January ramp-up plan, KPI dashboard, outsourced accounting, payroll funding, Q1 operating plan, small business tax planning December, tax filing services, W-2 verification, W-9 collection, year-end accounting tips



